CALYCANTHINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26N4
Molecular Weight	346.4686
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CC[C@@]23[C@@H]4NC5=C(C=CC=C5)[C@]2(CCN4C)[C@@H]1NC6=CC=CC=C36

InChI

InChIKey=XSYCDVWYEVUDKQ-GXRSIYKFSA-N

InChI=1S/C22H26N4/c1-25-13-11-22-16-8-4-5-9-17(16)23-19(25)21(22)12-14-26(2)20(22)24-18-10-6-3-7-15(18)21/h3-10,19-20,23-24H,11-14H2,1-2H3/t19-,20-,21-,22-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H26N4
Molecular Weight	346.4686
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12831783 | https://www.henriettes-herb.com/eclectic/usdisp/calycanthus.html | https://www.sciencedirect.com/science/article/pii/S0095955315305564

Calycanthine is the principal alkaloid of the family Calycanthaceae. Calycanthine is a central nervous system toxin, causing convulsions in animals. Calycanthine may mediate its convulsant action predominantly by inhibiting the release of the inhibitory neurotransmitter GABA as a result of interactions with L-type Ca(2+) channels and by inhibiting GABA-mediated chloride currents at GABA(A) receptors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
gamma-aminobutyric acid secretion 1 Target ID: GO:0014051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12831783	Inhibitor 8297
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12831783	Blocker 537	42.0 µM [IC50]
GABA-A receptor; alpha-1/beta-2/gamma-2 27 Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12831783	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Convulsant actions of calycanthine.	2003 Jul 1	12831783
Concise total synthesis of (-)-calycanthine, (+)-chimonanthine, and (+)-folicanthine.	2007	17415735
Chemical constituents from leaves of Palicourea coriacea (Rubiaceae).	2008 Jul	18404310
Antifungal activity of alkaloids from the seeds of Chimonanthus praecox.	2009 Jun	19551726

Patents

Sample Use Guides

In Vivo Use Guide

Median lethal dose of calycanthine in rodents: 43.79 mg/kg for mice, 17.16 mg/kg for rats

Route of Administration: Intravenous

In Vitro Use Guide

Calycanthine hydrochloride (10 uM), which did not alter nervous conduction in pre- and post-synaptic fibers, significantly reduced the efficacy of the synaptic transmission in giant axons of the cockroach (Periplaneta americana).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:04:18 GMT 2023` Edited by `admin` on `Sat Dec 16 09:04:18 GMT 2023`
Record UNII	F62N8QPR7V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CALYCANTHINE

Common Name

English

(4BS,5R,10BS,11R)-5,6,11,12-TETRAHYDRO-13,18-DIMETHYL-5,10B:11,4B-BIS(IMINOETHANO)-DIBENZO(C,H)(2,6)NAPHTHYRIDINE

Systematic Name

English

D-CALYCANTHINE

Common Name

English

(+)-CALYCANTHINE

Common Name

English

NSC-99016

Code

English

CALYCANTHINE [MI]

Common Name

English

5,10B:11,4B-BIS(IMINOETHANO)DIBENZO(C,H)(2,6)NAPHTHYRIDINE, 5,6,11,12-TETRAHYDRO-13,18-DIMETHYL-, (4BS,5R,10BS,11R)-

Systematic Name

English

Code System Code Type Description

CHEBI

3333